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Cyclopropylamine → (2-Chloro-9-fluoro-3-phenylpyrimido[1,2-b]indazol-4-yl)cyclopropylamine

HRID 877053
Notes
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Reaction equation

HRID 877053 reaction equation
[Cl:1][C:2]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14](Cl)[N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]3)=[C:4]2[N:3]=1.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>CN(C=O)C>[Cl:1][C:2]1[C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:14]([NH:26][CH:23]2[CH2:25][CH2:24]2)[N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]3)=[C:4]2[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 867025232,4-Dichloro-9-fluoro-3-phenylpyrimido[1,2-b]indazole

Product 1

HCID 86702530(2-Chloro-9-fluoro-3-phenylpyrimido[1,2-b]indazol-4-yl)cyclopropylamineYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1 g (7.5 mmol) 2,4-Dichloro-9-fluoro-3-phenylpyrimido[1,2-b]indazole (intermediate example Int-1-0, step 2) and 430 mg (8.4 mmol) cyclopropylamine were dissolved in 8.4 mL DMF and heated in the microwave for 20′ at 100° C. The solvent was evaporated and the residue was purified by chromatography on silicagel (eluents: dichloromethane/methanol) to yield 560 mg (52.7%) of the desired compound.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on silicagel (eluents: dichloromethane/methanol)

Sources & evidence

ORD record
ord-e0193c857f0b4dc69b3dd499d4e06351
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987286B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes